以氢硅烷为氢源: 铱催化N-杂环化合物的氢化

doi:10.6023/cjoc202110041

有机化学 ›› 2022, Vol. 42 ›› Issue (4): 1170-1178.DOI: 10.6023/cjoc202110041 上一篇下一篇

研究论文

以氢硅烷为氢源: 铱催化N-杂环化合物的氢化

张苗苗, 韩波^*(), 马豪杰, 赵亮, 王记江, 张玉琦^*()

延安大学化学与化工学院新能源新功能材料重点实验室陕西省化学反应工程重点实验室陕西延安 716000

收稿日期:2021-10-29 修回日期:2021-11-26 发布日期:2021-12-15
通讯作者: 韩波, 张玉琦
基金资助:
国家自然科学基金(22061041); 陕西省自然科学基金(2020JQ-789); 陕西省科技资源开放共享平台(2021PT-004); 延安大学博士科研启动经费(YDBK2019-60); 陕西省大学生创新创业训练计划(S202010719114)

Hydrosilanes as Hydrogen Source: Iridium-Catalyzed Hydrogenation of N-Heteroarenes

Miaomiao Zhang, Bo Han(), Haojie Ma, Liang Zhao, Jijiang Wang, Yuqi Zhang()

Laboratory of New Energy ＆ New Function Materials, Shaanxi Key Laboratory of Chemical and Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an, Shaanxi 716000

Received:2021-10-29 Revised:2021-11-26 Published:2021-12-15
Contact: Bo Han, Yuqi Zhang
Supported by:
National Natural Science Foundation of China(22061041); Natural Science Foundation of Shaanxi Province(2020JQ-789); Open Sharing Platform for Scientific and Technological Resources of Shaanxi Province(2021PT-004); Doctoral Research Foundation of Yan'an University(YDBK2019-60); Training Program of Innovation and Entrepreneurship for Undergraduates of Shaanxi Province(S202010719114)

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摘要/Abstract

发展了一种铱/氢硅烷/甲醇的催化体系, 不使用任何外加配体和碱的情况下, 实现了以喹啉化合物为代表的芳香杂环的选择性氢化, 得到了一系列1,2,3,4-四氢喹啉及杂环类化合物. 该反应操作简单, 以廉价且稳定的氢硅烷为氢源, 避免了使用危险易发生爆炸的氢气. 同时, 该体系对溴、氯、氟、酯、羧酸、氰基和硝基等官能团具有良好的兼容性. 该催化体系为制备各种1,2,3,4-四氢喹啉衍生物提供了一种方便、环保、实用的策略.

关键词: 氢化, N-杂环化合物, 铱, 氢硅烷

A ligand- and base-free method for the catalytic synthesis of bioactive 1,2,3,4-tetrahydroquinolines via the homogeneous iridium-catalyzed hydrogenation of quinolines and related N-heteroarenes is reported. A catalytic reduction of N-heteroarenes employing low-cost and air-stable hydrosilane was demonstrated under mild conditions. This reaction is scalable and tolerable for sensitive functional groups, such as bromide, chloride, fluoride, ester, carboxylic acid, cyanogroup and nitro groups. This catalytic system provides a convenient, environmentally friendly and practical method to obtain a variety of 1,2,3,4-tetrahydroquinoline derivatives under mild reaction conditions.

Key words: hydrogenation, N-heteroarenes, iridium, hydrosilane

引用此文

张苗苗, 韩波, 马豪杰, 赵亮, 王记江, 张玉琦. 以氢硅烷为氢源: 铱催化N-杂环化合物的氢化[J]. 有机化学, 2022, 42(4): 1170-1178.

Miaomiao Zhang, Bo Han, Haojie Ma, Liang Zhao, Jijiang Wang, Yuqi Zhang. Hydrosilanes as Hydrogen Source: Iridium-Catalyzed Hydrogenation of N-Heteroarenes[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1170-1178.

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图/表 7

Figure 1. Examples of bioactive drugs and candidates bearing 1,2,3,4-tetrahydroquinoline moiety

Scheme 1. Reported examples of hydrogenation of quinolines

Entry^a	[Si]—H (equiv.)	Solvent	T/℃	of 2a^b/%
1	PMHS (4.0)	MeOH	r.t.	55
2	(EtO)₃SiH (4.0)	MeOH	r.t.	40
3	Et₃SiH (4.0)	MeOH	r.t.	59
4	Ph₃SiH (4.0)	MeOH	r.t.	61
5	Ph₂SiH₂ (4.0)	MeOH	r.t.	66
6	PhSiH₃ (4.0)	MeOH	r.t.	74
7	PhSiH₃ (4.0)	EtOH	r.t.	71
8	PhSiH₃ (4.0)	ⁱPrOH	r.t.	46
9	PhSiH₃ (4.0)	THF	r.t.	39
10	PhSiH₃ (5.0)	MeOH	r.t.	71
11	PhSiH₃ (3.0)	MeOH	r.t.	68
12	PhSiH₃ (2.0)	MeOH	r.t.	39
13	PhSiH₃ (4.0)	MeOH	45	94 (83)^c

Table 1. Reduction of quinoline using hydrosilanes with iridium Catalysts

Table 2. Substrate scope of quinolines with substitution patternsa,b

Table 3. Reduction of N-heteroarenesa,b

Figure 2. Reaction profile for iridium-catalyzed hydrogenation of quinolone

Scheme 2. Gram-scale reduction and control experiments

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以氢硅烷为氢源: 铱催化N-杂环化合物的氢化

Hydrosilanes as Hydrogen Source: Iridium-Catalyzed Hydrogenation of N-Heteroarenes

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